Leadership Gifts Officer

Collaborates Closely With: Head of School, Advancement Team, Trustees, Alumni, Parents, and Volunteers The Opportunity: What Will You Do & How Will We Partner? Vermont Academy seeks a strategic, relational, and highly motivated Leadership Gifts Officer to help advance one of the most important moments in the school’s history. As Vermont Academy approaches its 150th anniversary and launches the Where Vision Meets Purpose Campaign in support of Vision 2030, this role will help shape the philanthropic future of the institution. At Vermont Academy, advancement work is deeply relational. It is rooted in listening carefully, building authentic trust, and connecting donors to a compelling vision for young people and the future of the school. The Chief Advancement Officer will work closely with the Leadership Gifts Officer who will cultivate and steward meaningful partnerships with alumni, families, grandparents, and friends of Vermont Academy—helping supporters align their philanthropy with the mission, priorities, and long-term sustainability of the school. This role combines frontline fundraising, strategic planning, donor stewardship, and an understanding of campaign management. The ideal candidate is equally comfortable building relationships over time, executing sophisticated fundraising strategies, and helping coordinate the systems and momentum necessary for a successful comprehensive campaign. Working closely with the Chief Advancement Officer and Head of School, this individual will help drive leadership annual giving, work on bridging mid level donors into major donors, campaign planning, and endowment growth during a transformative chapter in Vermont Academy’s history. Your Core Responsibilities This is a full-time, 12-month administrative position with significant travel (75%) and active engagement in school life. Major Gifts & Relationship Management Manage and strategically advance a dynamic portfolio of approximately 100–125 major gift prospects and donors, including alumni, current parents, parents of alumni, grandparents, and friends of the school. Develop and implement individualized cultivation, solicitation, and stewardship strategies designed to deepen engagement and secure philanthropic support, primarily in the $10,000–$50,000 range, while also supporting select six-figure opportunities. Identify, qualify, and build the major gift pipeline through prospect research, referrals, relationship mapping, and ongoing engagement strategies. Conduct meaningful donor conversations that connect Vermont Academy’s mission, strategic priorities, and student experience to philanthropic investment opportunities. Arrange, prepare for, staff, and follow up on donor meetings involving the Head of School, Chief Advancement Officer, trustees, and other key school leaders. Develop a deep understanding of Vermont Academy’s academic programs, student life, strategic plan, and institutional priorities in order to articulate a compelling case for support. Campaign Leadership & Strategic Advancement Partner closely with the Chief Advancement Officer on the planning and execution of the Where Vision Meets Purpose Campaign and other strategic fundraising initiatives. Support campaign planning efforts including prospect strategy, timelines, donor communications, cultivation events, volunteer coordination, and proposal development. Help coordinate leadership giving strategies tied to annual, capital, endowment, deferred, and non-cash gifts. Conduct and oversee prospect research for campaign and leadership-giving priorities, including research on newly enrolled families and emerging donor opportunities. Collaborate with the Director of Annual Giving and the Alumni Engagement Officer to ensure thoughtful donor movement and coordinated engagement across giving levels. Analyze giving trends and prepare reports, updates, and prospect strategy materials for senior leadership and Board committees. Maintain accurate and strategic documentation of donor engagement and solicitation activity within Advancement’s database, utilizing Blackbaud Raisers Edge and related systems. Stewardship & Donor Experience Lead thoughtful stewardship efforts for leadership and major donors, including those supporting endowed or named funds. Partner with the Advancement team to create annual impact reports, campaign updates, stewardship materials, and personalized donor communications. Ensure donors experience consistent, meaningful recognition and engagement through events, reporting, outreach, and ongoing relationship management. Help foster a culture of gratitude, professionalism, and responsiveness throughout the Advancement Office. Community Engagement & School Partnership Participate actively in school life, including attendance at major events, performances, athletic competitions, assemblies, and community programming. Recognize that advancement work is most effective when grounded in authentic connection to the daily life of the school. Serve as a collaborative and mission-aligned partner across departments and constituent groups. Support additional Advancement initiatives and special projects as needed. The Vermont Academy Team Member: Who Are You? You are: A compelling relationship-builder who leads with warmth, authenticity, and professionalism. A strategic thinker who can balance long-term vision with disciplined execution. A highly organized self-starter who thrives in a fast-moving, entrepreneurial environment. A collaborative colleague who values teamwork, trust, and shared purpose. A strong communicator who can tell the Vermont Academy story with clarity, confidence, and heart. Someone energized by building meaningful partnerships in support of transformational student experiences. You bring: Minimum of 5 years of advancement or fundraising experience, preferably in independent schools, higher education, or mission-driven nonprofits. Demonstrated success in major gifts, leadership giving, campaign strategy, and donor stewardship. Strong understanding of fundraising operations, prospect management, and moves management strategy. Exceptional written, verbal, and interpersonal communication skills. Experience with Advancement CRM systems such as Raiser’s Edge, Advancement NXT, Boost, or similar platforms. Strong organizational skills with the ability to manage multiple priorities and relationships simultaneously. Sound judgment, discretion, and professionalism when handling confidential information. Willingness to travel extensively and work evenings and weekends as needed. About Vermont Academy: Who Are We? Founded in 1876, Vermont Academy is a small New England boarding and day school nestled in the foothills of the Green Mountains. Rooted in four pillars—Land, Community, Ingenuity, and Independence—VA blends rigorous academics with outdoor education, innovation, and a profound sense of belonging. Our students are encouraged to be true to their best selves; our educators create space for students to lead, explore, create, and thrive. We teach by doing. We believe knowledge cannot change the world if it is left inside a book. Personalized education is not a luxury—it is what prepares students to shape a better future. Building toward Vision 2030 and our 150th Anniversary Campaign, Vermont Academy is investing boldly in: Experiential and applied learning Student wellness and healthy excellence Entrepreneurial and environmental programming Revenue-driving campus improvements Community, belonging, and transformational student experiences Our Commitment to Belonging Vermont Academy actively seeks to build and sustain an inclusive and equitable working and learning environment. We believe every team member enriches our community by bringing a broad range of identities, perspectives, and experiences to the work of teaching and learning. We value the whole person and strive to reflect that in how we work, live, and grow together. Compensation Full-time hybrid, 12-month administrative position. Salary Range: $85,00 - $95,000. Benefits include health insurance, retirement plan, and meals when school is in session. This is a non-housed, hybrid campaign position. Remote work for applicants living in the Greater Boston or the Tri-state (CT/NY/NJ) Metropolitan region, will be strongly considered. #J-18808-Ljbffr